While factors like local relevance, link building and trust seem to get all the attention these days, there are some ranking factors that you need to learn how to use effectively if you want to become a top-notch SEO.
The following ranking factors have proven to be equally important to the other factors. Continue Reading

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My question is this: what should come first, freshness or quality?
Neil brings up a great point by pointing out freshness, but what should take precedence? Should you focus on enhancing one large, greatly insightful piece of content, or should you consistently write about that topic? What's a better investment of your time and what has the most ROI for SEO?
Sorry for so many questions, but I've been holding them in since the freshness update a month or so ago. Would love to hear anyone's insight on this topic.

Personally, I go with quality first. However, I have seen sites succeed with content marketing and SEO that's very focused on freshness. If you are in a news vertical or focus on SERPs where fresh is the rule (e.g. https://www.google.com/search?q=30+rock+thursday) putting fresh first may help.

Using your specific comparison...
"Should you focus on enhancing one large, greatly insightful piece of content, or should you consistently write about that topic?"
... I'd actually do a mix. If the subject has enough depth for you to dedicate a category (or even a whole blog) to it, each post is an opportunity for you to get links, show Google you have fresh content, and promote something relevant but different on your social channels (as opposed to tweeting "just updated my _____ guide" so many times people start to ignore it). Many separate posts also allow you to better target a range of long-tail keywords.
At the same time, consolidating all of your content around a subject into a single, more organized and cohesive format provides you with a valuable information product (you don't have to sell it, but instead use it's value to overcome resistance to some action you desire from your readers, like signing up for a newsletter) that has potential to rank for a higher-volume keyword. Your mini posts can reference this piece of content regularly, and once-per-month update announcements can even be another regular post type.
Examples of this strategy can be seen with InsideFacebook.com and the Facebook Marketing Bible. Or SEOmoz's blog, where frequent fresh posts (which at SEOmoz's scale are high-quality pieces of content by themselves) regularly reference mega-content like the Search Ranking Factors or Beginner's Guide to SEO.

We've focused on deep, high-quality content and it consistently drives traffic. But we're in a vertical where freshness may not play as much of a role. We'll be testing more fresh content development/marketing in the future, however, so we'll see how it plays out.